For most of the last 50 years, nearly every U.S. president has negotiated secretly with the government of Cuba in bids to resolve the two nations' conflicts

In late August of 1994, the Nobel Prize—winning novelist Gabriel García Márquez traveled to Martha's Vineyard for a dinner with President Bill Clinton. "Gabo wanted to come and talk to Clinton about Cuba," recalled Rose Styron who, along with her famous husband, William, hosted the evening at their rambling island home. Indeed, the dinner party served as an elaborate cover for García Márquez to deliver a message to Clinton from Fidel Castro. While the other guests ate fried chicken with rice and gravy, the writer shared with the president details of Castro's proposal to end the "balsero crisis"—the flood of Cubans taking to the seas in small boats, inner tubes and makeshift rafts to cross the Florida Straits to the United States. As Rose Styron remembers, García Márquez also took the opportunity to press Clinton on "the need to open up relations" with Cuba; Clinton, she said, appeared to agree. "Try and come to an understanding with Fidel, as he has a very good opinion of you," García Márquez advised the president. The next day, García Márquez left the Vineyard and traveled to Havana to report on Clinton's response to Castro.

This furtive communication between a U.S. president and the fiery Cuban leader was no historical anomaly. Clinton was hardly the first U.S. president to negotiate with Castro, discreetly, through an intermediary. It is a little-known fact that since the Eisenhower administration broke relations with Cuba on January 3, 1961, every president has engaged in some form of dialogue with Fidel Castro—with the exception of George W. Bush. From Kennedy to Clinton, one U.S. administration after another has negotiated immigration accords, anti-terrorism treaties, counter-narcotics agreements and other bilateral arrangements. Behind the scenes, the United States and Cuba have repeatedly resorted to clandestine diplomacy to address and resolve crises, ranging from tensions at the U.S. military base at Guantánamo to terrorist plots against Cuba. Several presidents—most notably Kennedy, Ford and Carter—engaged in secret dialogues with Castro to explore the normalization of relations.

This history has immediate relevance for the new president of the United States. During his campaign, Barack Obama raised expectations about a change in Cuba policy when he pledged to meet with leaders of hostile states such as Iran and North Korea "without preconditions." Asked during a debate with Hillary Clinton in Texas if he would actually sit down with Raúl Castro in Cuba, Obama replied:

That's correct.... I would meet without preconditions, although Senator Clinton is right that there has to be preparation.... And that preparation might take some time. But I do think that it's important for the United States not just to talk to its friends, but also to talk to its enemies. In fact, that's where diplomacy makes the biggest difference.
Preparations for such diplomacy should include a review of past efforts by Obama's predecessors to talk with Fidel about changing the hostile framework of relations that has endured for 50 years. Kennedy, Ford and Carter failed to reach an accommodation with Cuba. Clinton's efforts to reduce tensions and improve relations also fell short of that goal. But the historical record generated by their administrations contains important lessons on how an effective effort at direct diplomacy might end, once and for all, the perpetual antagonism in U.S.-Cuban relations.

JFK AND CASTRO

In his youthful demeanor and charisma, Obama has often been compared to John F. Kennedy. The Cuban issue dominated Kennedy's thousand days in office. As president, he led the country and the world through the Cuban Missile Crisis; he also oversaw some of the most egregious acts of U.S. aggression toward the island nation, including the failed Bay of Pigs invasion, the trade embargo and Operation Mongoose, a set of covert actions designed to destabilize the country and overthrow Castro. But Kennedy also had the courage and curiosity to explore what Top Secret National Security Council memoranda described as "U.S./Cuban discussions about accommodation" and "a rapprochement with Castro."

Early in his administration, Kennedy learned that the Cubans were open to such talks. During an international economic summit in Montevideo, Uruguay, in August 1961, Che Guevara arranged an all-night meeting with White House aide Richard Goodwin—by using an Argentine diplomat as an intermediary to dare Goodwin to smoke a Cuban cigar. Che emphasized several salient points that would be repeated in almost all future negotiations and remain relevant today.

First, as Goodwin wrote in a secret memorandum of conversation to President Kennedy, Cuba was clearly interested in a dialogue that would lead to coexistence. "They would like a modus vivendi—at least an interim modus vivendi," Goodwin reported. Second, although Castro was willing to make a number of concessions toward that goal, the nature of Cuba's political system was nonnegotiable. "He said they could discuss no formula that would mean giving up the type of society to which they were dedicated." Finally, Guevara raised the issue of how the two countries would find "a practical formula" to advance toward an accommodation. He made a pragmatic suggestion—one that Cuba would invoke again and again in pressing for a diplomatic dialogue over the next 48 years: "He knew it was difficult to negotiate these things but we could open up some of these issues by beginning to discuss secondary issues … as a cover for more serious conversation."

To demonstrate just how serious the Cubans were, Che gave Goodwin an engraved mahogany box of premium Cuban cigars for Kennedy—a gift representing Cuba's first attempt, although not its last, at "cigar diplomacy" aimed at a U.S. president.

When Goodwin returned to Washington, he recommended seeking "some way of continuing the below ground dialogue which Che has begun." He even tasked the CIA to develop a "precise, covert procedure for continuing below ground dialogue with the Cuban government" to maintain secrecy around such politically sensitive talks. But the rest of the administration ignored Cuba's overture. "The emotion that had always surrounded the 'problem' of Cuba had, if anything, been heightened by our defeat at the Bay of Pigs," Goodwin later wrote. "To make a deal with Castro, any kind of deal, would have been politically difficult, perhaps impossible."

Yet, in early 1963, when U.S. intelligence picked up signals of a breach in Soviet-Cuban relations in the aftermath of the October 1962 Cuban Missile Crisis, savvy administration officials saw an opportunity and an opening for an accommodation with Castro. The idea of using "the sweet approach" to advance the possibility of "quietly enticing Castro over to us" began to surface in Top Secret NSC memoranda. Alongside proposals for covert intervention and sabotage in Cuba, senior White House aides proposed exploring "the rapprochement track." Kennedy "clearly thought this was an exploration worth making," his NSC adviser, McGeorge Bundy, recalled in an interview with the authors. The key problem, Bundy said, was finding a politically "non-dangerous way" to pursue a dialogue.
Starting in the spring of 1963, the Kennedy administration engaged Castro in a dialogue through three intermediaries. James Donovan was the first. A prominent New York lawyer and renowned international negotiator, Donovan was recruited by Attorney General Robert F. Kennedy to win the release of 1,113 Bay of Pigs brigade members who had been captured during the invasion debacle. In face-to-face talks with Castro between August and late December 1962, Donovan not only succeeded at obtaining the release and repatriation to the United States of the Cuban exiles, but thousands of their relatives as well. In Donovan, Castro found the first trusted—indeed respected—U.S. emissary. Believing that the prisoner negotiations had set the stage for a broader discussion about U.S.-Cuban relations, Castro broached the subject in mid-March 1963. "If any relations were to commence between the U.S. and Cuba," Fidel wanted to know, "how it would come about and what would be involved?" In his debriefing at the CIA—tape-recorded and later transcribed—Donovan reported his colorful response:

So I said to him, well, do you, are you familiar with porcupines, and this had to be translated … but they finally agreed that he did understand porcupines. So I said, now do you know how porcupines make love? And he said no. And I said well, the answer is "very carefully," and that is how you and the U.S. would have to get into this.

Castro's expressed interest in discussing peaceful coexistence set off the first high-level debate inside the U.S. government over how or even whether to respond. In a Top Secret—Eyes Only option paper to the White House, the State Department's Cuba specialist, Robert Hurwitch, suggested that Donovan be instructed to "take a week-long walk on the beach" with Castro and tell him that Cuba's ties to the Sino-Soviet bloc were nonnegotiable and would have to be broken. Surprisingly, President Kennedy overruled this approach as too restrictive. "The President does not agree," McGeorge Bundy wrote in a Top Secret memo. "We don't want to present Castro with a condition that he obviously cannot fulfill. We should start thinking along more flexible lines."

Talks with Castro continued through a second, unlikely intermediary: a striking blonde reporter from ABC News named Lisa Howard. During Donovan's last trip to Havana in April 1963, Howard begged him to undertake one final mission—to negotiate an interview with Castro for ABC. Howard scored an exclusive televised interview with the Cuban leader— his first with a U.S. network in four years.
Castro used the interview to make the same point he made with Donovan. The prisoner negotiations could be "a beginning point for discussions, if the United States wants it, it is the beginning of better relations." The hour-long interview, broadcast on May 10, 1963, generated headlines around the nation such as "Castro would like to talk to Kennedy" and "Castro Makes Overt Hints He Wants Kennedy Parlay."

Behind the scenes, Lisa Howard committed herself to making negotiations happen. When she returned from Cuba, she briefed Deputy CIA Director Richard Helms on her private talks with Fidel. "Howard definitely wants to impress the U.S. government with two facts: Castro is ready to discuss rapprochement and she herself is ready to discuss it with him if asked to do so by the U.S. Government," Helms reported in a Top Secret memorandum of conversation to President Kennedy.

Howard also made contact with a fellow journalist-turned-diplomat, William Attwood, who was special adviser to U.N. Ambassador Adlai Stevenson. The two worked out a "cocktail diplomacy" scheme. Howard would hold a reception at her Central Park East townhouse and invite both Cuba's ambassador to the U.N., Carlos Lechuga, and Attwood to attend so they could discuss how to move negotiations forward. On September 23, amid drinks, finger foods and several dozen members of the New York literati, the first bilateral talks on the potential for a U.S.-Cuban accommodation took place. Lechuga hinted that Fidel was "indeed in the mood to talk," and "thought there was a good chance I might be invited to Cuba if I wished to talk to Castro," Attwood reported to the White House.

To sustain momentum for the diplomatic initiative, Howard transformed her home into a center of communications between Havana and Washington. She made, and received, a series of calls to Castro's office hoping to organize Attwood's trip. On October 31, Fidel's top aide, Rene Vallejo, called her and formally transmitted an invitation for Attwood to clandestinely travel to Cuba and meet with Castro alone.

Castro's concrete invitation set off a flurry of discussion inside the Oval Office. There, on November 5, Bundy briefed President Kennedy on Castro's proposal. The president's secret taping system captured his concern about how the secret mission would actually stay secret, but he expressed no opposition to the meeting itself. "How can Attwood get in and out of there very privately?" the president asked. Bundy and Kennedy then discussed the possibility of "sanitizing" Attwood—retiring him from his U.N. post for a month before undertaking the secret dialogue in Cuba.

On November 19 at 2 a.m., Attwood spoke to Vallejo himself from Lisa Howard's study. Before he could travel to Cuba, Attwood said, the Kennedy White House felt a preliminary meeting in New York "was essential to make sure there was something useful to talk about." Vallejo replied that Castro's office would send instructions to Lechuga on what "an agenda for a later meeting with Castro" would look like. When Attwood passed this information to Bundy later that day, he was told that when the agenda was received, "the President wanted to see me at the White House and decide what to say and whether to go [to Cuba] or what we should do next."

In the final days before his death, Kennedy used yet a third intermediary to send a message of potential détente to Castro. His emissary was the noted French journalist Jean Daniel, who, through Attwood, obtained a meeting with the president. Kennedy expressed some empathy for Castro's anti-Americanism, acknowledging that the United States had committed a number of sins in pre-revolutionary Cuba, including turning the island into "the whorehouse of the U.S." He told Daniel that the trade embargo could be lifted if Castro ended his support for leftist movements in the hemisphere, and that Daniel should return to Washington after seeing Castro and brief Kennedy. The U.S. president, Daniel thought, was "seeking a way out" of the poor state of relations with Cuba. "When I left him," Daniel recalled, "I had the impression I was a messenger of peace."
Daniel transmitted Kennedy's message during a meeting with Castro in Havana on November 20. "He listened to me intently. He was drinking my words," Daniel would recall in an interview 40 years later. "Clearly he was happy about the message I was delivering. Sometimes he would say, 'Maybe he has changed. Maybe things are possible with this man.'" Two days later, their subsequent meeting was interrupted by a phone call informing Castro that Kennedy had been shot. He turned to Daniel and said, "This is the end of your mission of peace." Daniel recalled thinking that he was right: without Kennedy, there was no mission.

KISSINGER'S CARIBBEAN DÉTENTE

As Obama's foreign policy aides review the actions of his predecessors to engage Castro in a dialogue toward better relations, they will note the bipartisan nature of this history. Republican and Democratic presidents alike have talked with Castro. At the end of the Nixon administration and throughout the short presidency of Gerald Ford, the United States pursued a secret effort to negotiate normal relations.

This initiative began on April 24, 1974, at 2:32 p.m., with a phone call to Secretary of State Henry Kissinger from Frank Mankiewicz, a longtime Democratic Party operative and former press secretary for Robert Kennedy. "That trip I told you about is now on … to the Caribbean," as Kissinger's secret taping system recorded Mankiewicz's cryptic remarks. "I told you that I might be doing a television interview with…." Kissinger replied immediately: "Yes, yes, I know exactly—of course. Good. Then I want to see you…. I must see you before you do that." Six weeks later, when Mankiewicz traveled to Havana along with two other journalists, he carried with him a handwritten note from Kissinger to Castro. The secret communication stated that Kissinger was interested in initiating bilateral talks on mutual interests but that such a dialogue needed to be conducted discreetly, through intermediaries and unofficial meetings. Castro deemed the note "a very serious communication" and sent a message back with Mankiewicz, along with a box of premium Cuban cigars. (When a U.S. Customs guard attempted to confiscate the cigars, Mankiewicz issued a stern warning: "Son, this box of cigars is a personal gift for Secretary of State Henry Kissinger. Are you sure you want to take them away?")

So began the first serious dialogue aimed at fundamentally changing the framework of U.S.-Cuban relations—a dialogue that holds significant lessons for the new Obama administration. As is the case today, in the mid-1970s the domestic and international controversy over the hostile nature of U.S.-Cuba policy was proving to be a greater headache for the executive branch than the regime in Cuba itself. In the U.S. Congress, there was a growing bipartisan consensus that the trade embargo should be lifted. In the Organization of American States, the Latin American nations were pushing to lift the ban on diplomatic and economic relations with Cuba that Washington had strong-armed them into approving in 1964.

Given these domestic and international pressures, a secret State Department review of Cuba policy, titled "Normalizing Relations with Cuba," recorded the clear advantage to moving toward better bilateral ties:

If there is benefit to us in an end to the state of "perpetual antagonism" it lies in getting Cuba off the domestic and inter-American agendas—in extracting the symbolism from an intrinsically trivial issue.… Our interest is in getting the Cuba issue behind us, not in prolonging it indefinitely.

Negotiations to change the hostile nature of U.S.-Cuban relations should take place as quickly as possible, the report concluded, before Congress and the OAS took away Washington's bargaining leverage. "We have a poor hand to play and should ask for a new deal before we lose our last chip."

It was in the context of these political realities that Kissinger initiated contact with Castro. He authorized his top deputy, Lawrence Eagleburger, and William D. Rogers, the assistant secretary of state for inter-American affairs, to undertake half a dozen furtive meetings with Castro's representatives in airport cafeterias, swanky New York hotels and personal homes. Kissinger made his negotiating philosophy clear: "It is better to deal straight with Castro," he told his aides. "Behave chivalrously; do it like a big guy, not like a shyster. Let him know: We are moving in a new direction; we'd like to synchronize…; steps will be unilateral; reciprocity is necessary."

At the first meeting, held in a public cafeteria at LaGuardia Airport on January 11, 1975, Kissinger's aides came well prepared. An aide-mémoire Eagleburger read to Cuba's U.N. ambassador, Ramón Sánchez-Parodi, and his deputy, Nestor Garcia, was explicit in the goals of the dialogue: "explore the possibilities for a more normal relationship between our two countries." Kissinger made clear the potential for a U.S.-Cuban détente:

The ideological differences between us are wide. But the fact that such talks will not bridge the ideological differences does not mean that they cannot be useful in addressing concrete interests which it is in the interest of both countries to resolve. The United States is able and willing to make progress on such issues even with socialist nations with whom we are in fundamental ideological disagreement, as the recent progress in our relations with the Soviet Union and the People's Republic of China has shown.

The United States set no preconditions for these talks. Unlike his predecessors, Kissinger did not demand that Cuba terminate its military ties with the Soviet Union, and unlike his successors, he did not make democratization or human rights a prerequisite or even a goal of settling the differences in U.S.-Cuban relations. Sánchez-Parodi, however, suggested that Cuba might have a precondition of its own—lifting the trade embargo. He promised to report back to his government.

To underscore Washington's commitment to negotiations, the State Department immediately undertook a series of diplomatic gestures. In mid-January, Assistant Secretary Rogers quietly arranged for the 25-mile travel restriction on Cuban diplomats to be expanded to 250 miles, so that Cuba's U.N. officials could travel to Washington for secret meetings in the future. The United States lifted prohibitions on American corporations making sales to Cuba through third-country subsidiaries. And Kissinger sent another secret message to Castro through Frank Mankiewicz alerting him that these measures reflected U.S. interests in continuing to explore more normal relations and suggesting another meeting.
But Cuba did not respond to a request for another meeting until June, when U.S. officials again approached the Cuban delegation at the U.N. and requested a "further government-to-government exchange of views" before the OAS convened in San José, Costa Rica, in late July to vote to lift multilateral diplomatic and trade sanctions. At a meeting at Eagleburger's home in Washington, D.C., on June 30, the two sides planned a major secret negotiating session at the Pierre Hotel in New York.

On July 9, Eagleburger, Rogers, Sánchez-Parodi and Garcia quietly gathered in a private room at the Pierre for what, at that point, would be the most significant and serious negotiating session in U.S. relations with Castro's revolutionary government. According to a declassified transcript of the meeting, Assistant Secretary Rogers laid out the U.S. proposal for a series of steps by both countries culminating in normal relations. Washington was prepared to lift the embargo piece by piece if Cuba reciprocated by: releasing American citizens in Cuban jails; allowing family travel to and from the island; restricting military relations with the Soviet Union; committing to nonintervention in Latin America; settling U.S. property claims from seizures after the revolution; and tempering support for Puerto Rican independence movements.

But, with the exception of family travel, the Cubans were not willing to yield on any of these points. Sánchez-Parodi pointed out the irony of Washington demanding that Cuba commit itself to nonintervention in the region amid recent revelations of CIA covert intervention in Chile contributing to the September 11, 1973, overthrow of the democratically elected president, Salvador Allende. On Puerto Rico, he said, Cuba believed in the "need for independence and self-determination." Once again, he indicated that lifting the embargo was a precondition for Cuba to engage in serious negotiations. "We are willing to discuss issues related to easing the blockade but until the embargo is lifted, Cuba and the United States cannot deal with each other as equals and consequently cannot negotiate." The meeting ended rather abruptly with Eagleburger rushing to catch the Eastern Airlines shuttle back to D.C.
The momentum for any progress in future talks came to a complete halt in September. First, Castro convened a special conference on Puerto Rican independence in Havana, casting the United States as a neocolonial imperialist power. Then, in November, Cuba deployed thousands of combat troops into Angola to support the MPLA government of Agostino Neto, who had requested assistance against CIA- and South African—backed rebels fighting to control Angola's post-colonial future. The Cuban deployment marked Castro's first major military foray into Africa and established Cuba as a leading player in the Third World.
The audacity of a small island nation in the U.S. sphere of influence challenging U.S. geostrategic aims in Africa left Kissinger apoplectic. "I think we are going to have to smash Castro," he told President Ford according to a recently declassified memorandum of conversation. "We probably can't do it before the [1976] elections." For the final meeting with the Cubans held at Washington National Airport on January 12, 1976, Kissinger sent Assistant Secretary Rogers with a somewhat more diplomatic message: "Cuba's dispatch of combat troops to take part in an internal conflict between Africans in Angola is a fundamental obstacle to any far-reaching effort to resolve the basic issues between us at this time."

The major legacy of Kissinger's initiative was that it took place, thereby setting the stage for the next president. When Jimmy Carter won the November 1976 election, Frank Mankiewicz briefed his secretary of state designate, Cyrus Vance, on the secret dialogue during the Ford administration. The Carter administration came into office prepared to pick up where the Kissinger team had left off.